Things To Do
Lucky Catch Cruises
Jen (Drew's mom): Take a scenic cruise of Portland harbor. With Lucky Catch you can see up close an personal how our tasty red friends get from the bottom of the ocean and onto your dinner plate.
Run or Walk the Local Trails
Cousin Amber: Go check out the Back Cove Trail and the Eastern Prom Trail for any guests looking to get active.
Portland Head Light
Aunt Rose: An iconic Maine landmark located north of Portland in Cape Elizabeth. You can visit Fort Williams Park at 1000 Shore Road to see one of the oldest operating lighthouses in America, as well as take in the stunning Maine coastline.
DiMillo's On the Water
Ron (Drew's grampy): DiMillo’s On the Water is one of Portland, Maine’s most iconic dining experiences - serving up fresh seafood on a floating restaurant set aboard a converted car ferry docked in the city’s harbor.
Breakfast at Marcy's Diner
Cousin Hank: Becky's is for tourists.
Visit Portland Observatory
Uncle Kenny: Once a maritime signal tower, this seven-story tower operates as a museum, offering visitors sweeping panoramic views of the harbor and a glimpse into the city’s seafaring past.
Tour Allagash Brewing
Cousin Jack: Tour Allagash Brewery, one of Maine's most iconic beer brands known for pioneering Belgian-style beers in the United States.
Eat at Duckfat
Tommy (Drew's Brother): This is a cozy spot that serves fresh takes on well known comfort foods, including some of the best french fries you'll ever try. No reservations, and first-come-first-serve.
Sunset Wine Cruise
Aunt Jo: Get tickets to step aboard the immaculate 74-foot tall ship Frances for an incredible experience of enjoying fine wines while sailing on the pristine Casco Bay, with Sommelier Erica Archer as your guide. Summer is a magical time of year in Portland, Maine.
Eat at Palace Diner
Eric (Drew's dad): If you find yourself looking for breakfast as you head south of Portland, check out Palace Diner in Biddeford, ME. It's in an old train car, and they make the best breakfast sandwich around.
Drink at The Porthole
Uncle Mike: If you're looking for cold beers and live music on the water, this is your spot.
Hike Pleasant Mountain
Aunt Pam: There are a few local hikes in the area. Pleasant Mountain is a great option just about an hour drive outside of Portland.